Roman's Hell
by DoctorOzpin
Summary: We all knew that Roman was going to Hell. What exactly is Hell for him anyway?
1. Arrival

"AND SURVIVE!" Roman screamed with a swing of his cane.

However Little Red was no longer on the ground before him. After completing his swing he also realized that everything around him had changed. For a moment he thought Neo come back and warped them somewhere. However upon looking around he couldn't find Neo.

More so was that everything around him had changed dramatically. The plagues of Grimm circling the borrowed Atlas ship had vanished. The metal hull beneath him had transformed into some form of dark rock with a thin film of fog rolling over his feet. The sky had become dark, moonless, and devoid of stars. The sounds of the raging battle of Beacon had ceased entirely.

"Where the hell am I?" Roman asked himself.

"You seem to already know the answer," a voice echoed from all around.

"Who the hell are you?" Roman demanded, spinning in search of the voice.

"I am a guide," the voice answered. "I am here to help you onto your path."

"Excellent, cause this place is pretty dark and I really found myself thinking 'Now where is the nearest road? I'd hate to be late for dinner.'"

"Do you realize where you are?"

"No. That's probably why I asked initially 'Where the hell am I?'"

"I misunderstood you. You see, you are in hell."

"Come again?"

"You are in hell."

"…You mean like… dead? Afterlife?"

"Yes."

"Huh, I didn't recognize it without the fire and brimstone. I was actually expecting Cinder to be the one to greet me but I guess I died first."

"Indeed. You seem to be taking this better than most."

Roman sat down on the cold stone ground. He let his cane roll away as he placed both hands behind him. He stared at the empty sky above and exhaled deeply.

"Heroes die," Roman said, "every single one of them. I guess I wasn't bad enough to avoid that."

"No, you were no hero."

"Hey, I'm having a cathartic moment and don't need your input."

"That's good, but there is no denying that you were a bad guy."

"No shit."

"As such you have been given a punishment to serve. As your guide I am instructed to take you there once you come to terms with the fact you died."

"So, right now?"

"Yes."

In an instant Roman found himself whisked away from the empty field. He found himself sitting on a bed freshly made. Three other beds aligned the room but it made the room very cramped. A single large window adorned the wall behind him and let light flood into the room. Along the other wall was a door.

"You know I don't think you guys really know how to make hell unenjoyable," Roman commented.

"Mr. Torchwick, what do you hate most?" the voice asked from all around.

"Ah nah nah, you won't trick me into telling you that. You're going to make changes to this world based on what I tell you."

"No, I have no power over this punishment. The job of making punishments goes to a different faction of demons. I do, however, have the specifications of your personal hell in front of me?"

"How can an omnipresent voice have something in front of them?"

"That's a matter beyond your capability to understand."

"Well for one I hate stuck up people like you."

"I could just read the list to you if you don't want to take this seriously."

"Fine," Roman conceded. He thought long and hard before continuing, "I hate most kids."

"Mhmm."

"I hate young love. So dumb how they have to beat around the bush one everything. I hate squirrels. Acorn bastards. Uh… let's see. Goody goodies piss me off. So what? Are you going to have me appease and romance an army of goody-goody squirrels?"

"Not quite. The final thing on your list of things you hate is not being able to speak your mind."

"That sounds about right. If I've got something to say I'll probably say it."

"As punishment for your crimes it has been decided that you will live out a dating simulation game."

"Come again?"

"For every Lien worth of property you've stolen, 'borrowed,' damaged, or destroyed you will complete one play through of said dating sim game."

"No…"

"Failure to romance any of the characters will not count as a play through. Romancing multiple characters will count as only one play through."

"Oh dust. Oh no, no, no. Please no. Anything else."

"As per dating sim format, you will only be allowed to progress along predetermined routes. As a gift, since you weren't the gravest sinner of your time, the variety of routes is quite open. The setting for your game will be Beacon Academy, modern era with all the Huntsmen and Huntresses you came to 'love' in your life of crime. You will be transferring into one of the teams that already existed at the time of your death. To make space for you we had to remove someone you never met."

"Wait, hold up, hell no, you can't make me. Wait. Uh… you said I had to play for how many times?"

"For every Lien worth of materials you stole or destroyed."

"Can uh… can I get a running total of that?"

"3, 465,732 Lien."

"Wow. Really? Only three and a half million. I'm pretty sure I blew up downtown Vale and a couple Atlas Command ships. Not that I'm complaining, but it seem… underwhelming."

"Something you're probably used to saying." The omnipresent voice muttered.

"What was that?" Torchwick accused.

"You are free to contact me with any questions or concerns. I will not tell you how to win the game, however."

"No, of course not. Heaven forbid anything good ever goes my way."

"Yes, Heaven does forbid it." The voice made as a final remark.


	2. Day One

Torchwick lay down on the bed. He shook his head as he tried to come to grips with reality. His current situation, living a dating sim, just felt so impossible. He knew he was in hell because of how he lived, but he admitted he'd do it all again given the choice.

A prompt suddenly appeared in front of Torchwick. It took him by surprise and he bolted upright. It was a blue message box that filled the majority of his vision. Torchwick looked around the room and noted the message box moved with his movements. It read:

 _Would you like to play the tutorial?_

 _-Yes_

 _-No_

Torchwick looked at the options and it didn't take him long to make a decision. He reached out a hand to tap "Yes." His hand simply passed through the option and nothing happened. He swatted at the option again to no avail.

"Yes I want – " Torchwick said.

"Welcome new player," a female voice began, interrupting Torchwick. "You have begun the tutorial. The purpose of this tutorial is to familiarize yourself with the mechanics of this game. What you do in the tutorial will not carry over to actual gameplay. Are you ready?"

Again a message box appeared in front of Torchwick. The options were:

 _-Yes_

 _-No_

"Yeah, I guess," Torchwick said.

Nothing happened. He sighed and tried to tap the "yes" option which still did nothing.

Torchwick corrected saying, "Yes."

"Excellent," the voice continued. "As you may be noticing, dialogue options will be limited at points in your play through. At these points you may only continue by repeating the provided dialogue options. Anything else you say will not be registered by the system or avatars. Outside such moments you are free to say whatever you want.

"This dating sim is very powerful and versatile. Your settings are Beacon and the town of Vale. This system allows open world exploration of your environments. Romantic encounters can occur at any time, of any day, in any place. It is up to you to find such encounters and capitalize them."

"You said open world?" Torchwick asked.

"To assist you in your romances," the voice said, ignoring the question, "we have provided you a small notebook. It will always exist in your front left pocket. Opening it is the only pause menu we will allow you. Inside you will find a data base of all the avatars you may romance. Until you encounter them in game their page in the notebook will remain blank. You are free to write any notes about each character on their page and the notes will save between play throughs.

"Here in Hell we do not take Romance lightly. To woo the hearts of these avatars you will need to get to know them, learn what they love, and win romance mini-games. Each avatar has a unique romance mini-game and the difficulty will of each encounter will increase as you progress along the affection tack. A successful play through is achieved when you win your first kiss with any romanceable avatar. Failure to do so in a years' time counts a failed play through.

"That said, do you have questions?" the voice finished.

"Yeah," Torchwick began. "You said open world, right?"

"Yes."

"How many romanceable girls are there?"

"There are thirteen romanceable female avatars."

"Is it possible to fail before the end of a year?"

"Yes."

"You said romance mini-games?"

"I did."

"The hell does that mean?"

"It's a game within a game."

"Wow, every part of hell is as sarcastic as I am," Torchwick said under his breath. "What kind of mini-games am I going to play? Bejeweled? Dust Crush?"

"The mini-game will depend on the avatar. It will reflect their personality, and knowing the avatar intimately may give you better odds of winning. Do you have any further questions?"

"Not really."

Torchwick's vision was filled with text. Massive cursive letters spelling "Day 1" appeared and slowly faded from view. Then the only door into the dorm opened. In walked three other people.

The one leading the three was a girl with a white shirt and pink skirt. She walked in and leapt onto the nearest bed which made her pink hair flail wildly. Behind her was a taller boy with long black hair wearing some green get-up Torchwick didn't know the name for. He paused in the doorway. Behind him was someone even a criminal Torchwick could name: Pyrrha Nikos.

"So, you're our new teammate?" Pyrrha asked.

Torchwick went to reply but the world somewhat faded. Three dialogue options scrolled into view. They read:

 _-I suppose I am_

 _-Yeah, my name is Roman._

 _-New? What happened to the old one?_

"Wow," Torchwick said. "I don't even get to introduce myself. Let's see here… I don't really care about the old teammate. I'm not some goody goody… Wow. I wouldn't say any of this. No choice then, 'I suppose I am.'"

"Yeah," Pyrrha continued. "Our old teammate, old leader, cheated his way into the school. He was – "

"Jesus I didn't pick the backstory option," Torchwick said.

"Excuse me?" Pyrrha asked, taken aback.

"Wait," Torchwick sat up, "You can hear me?"

There was a long silence before the other boy said, "We can all hear you."

"Aren't you a wise ass?," Torchwick returned.

"Does that make you the crazy one?" the girl asked.

"Listen here brat," Torchwick said turning to her.

"Wait," Pyrrha interjected. "Now, now, we don't need to start a fight. I think we're getting off on the wrong foot. I mean, we haven't even introduced ourselves. I'm Pyrrha Nikos."

There was a pause before the boy added, "I'm Lie Ren."

"I'm Nora," the girl said.

Torchwick sighed before saying, "I'm Torchwick."

"That doesn't start with an 'R'" Nora pointed out.

"Really?" Torchwick asked. "I hadn't noticed."

"Duh," Nora returned. "That isn't what I meant. Our team is Team Prune."

"Prune?" Torchwick asked.

"P-R-R-N," Ren spelled, "Prune."

"So," Nora continued, "What's your last name? The 'R' in our name."

Torchwick opened his mouth to speak but was interrupted by dialogue options.

"I'm really starting to hate this game," Torchwick muttered as he read his options.

 _-It's Roman._

 _-Actually it's my first name, and it's Roman._

 _-Roman._

"These are literally all the same," Torchwick said. "Why do I even have to pick? 'It's Roman', how is that even an option."

"How is what an option?" Pyrrha asked.

Torchwick realized what he'd done. He'd said one of the options sarcastically but the stupid game had taken him seriously. This was shaping up to make him look like an insane person.

"Nothing," Torchwick said.

"I guess those are introductions," Ren said. "We should go. Class starts soon."

"Oh right," Pyrrha said. "Roman, the team has the same schedule so just follow us."

"Sure," Torchwick said, "and I'd rather you call me Torchwick."

The next four hours were spent in lectures given by Professor Port and Oobleck. Torchwick had nearly fallen asleep in Port's class, but the fact they were in the first row incentivized staying awake. He'd tuned out Oobleck's entire lecture and instead thought about Neo and whether or not she was still alive. Finally it was lunch, and after that was his last class of the day with Professor Goodwitch.

The lunch was nothing special. He had a choice of soup, mystery meat, or a sandwich. He chose the sandwich at Pyrrha's suggestion. The four of them sat at a table and Nora jumped into recounting her dream last night. Something about fighting a giant Ursa that turned into a pancake demon.

"Hey Pyrrha," someone said, taking a seat across from Torchwick at the table. "Is this your new teammate?"

He looked up and his face contorted into that of disgust. Across from him in her childish little hood was Little Red. She was looking at him with the biggest and dumbest grin on her face. The grin faded as she realized Torchwick was giving her a death stare. She looked over to Pyrrha hurriedly and lost the smile.

"Torchwick," Pyrrha hissed. "Play nice."

"You're not my boss," Torchwick replied.

"But I am your leader," she retorted. "This is Ruby, and she is a _good_ friend"

"Neat, but she isn't my friend," Torchwick replied.

"Uh hehaha," Ruby forced a laugh. "Not super friendly huh? That's alright."

"Torchwick," Pyrrha said.

Torchwick was going to retort when his vision filled with dialogue options. He sighed as they became legible and he skimmed his options.

 _-Sorry Ruby._

 _-Sorry Pyrrha._

 _-No._

"Finally, an easy one," Torchwick said. "N- ... Wait. I'm supposed to be romancing these twerps. Almost forgot. No point in being nice to both of them if I don't have to. Let's see, 'Sorry Ruby.'"

"It's ok," Ruby said.

Three other people sat down at the table. Torchwick recognized each one of them: Ice Queen, Kitty Cat, and Blondie. Just looking at the four people across from him was a subtle reminder of the fact he was in hell; if he were in heaven he'd never see these faces again.

"So," Blondie began, "this is the new teammate. I'm Yang."

"Blake," Kitty Cat said.

"Weiss," Ice Queen added.

"Torchwick, Roman Torchwick," Torchwick replied.

"Mind if I call you Roman?" Yang asked.

"Greatly," Torchwick replied.

"Oh," Yang said with a smirk, "Do you not like Roman?"

"The last person who called me Roman was a massive bitch," Torchwick said.

"I called you Roman before we left the room," Pyrrha pointed out.

"Not you, the one before I came here," Torchwick corrected.

"Oh ho this is getting better," Yang said. "An old lover, an ex? Who was she?"

"Haha," Torchwick laughed genuinely, "My Oum there's no way we'd ever have anything like that. She'd sooner castrate me than consider a date."

"Castrate?" Ruby asked.

"I'm not going to explain that one," Torchwick suddenly very serious.

Ruby pulled out her scroll. After a quick search her face blushed a deep red.

"So you're that kind of guy?" Yang inferred.

"Yang!" Weiss, Pyrrha, Blake, Ren, and Ruby all said in unison.

"You read too much into that," Torchwick said.

"Stop that," a voice cried from behind them.

The group turned to see a rabbit faunus having her ears pulled on by a guy in armor. She was half bent over with the guy's hand firmly grasping her left ear. Her food had fallen from her tray. Torchwick could see the beginnings of tears in her eyes.

"See, I told you they were real," the guy said, giving the ears a yank.

Torchwick's vision filled with two choices:

 _-Intervene_

 _-Ignore_

"This is a romance game," Torchwick said, rising. "Not like I really care too much."

Torchwick made his way over to the bully and his compatriots. There were four of them and they all starred as Torchwick approached. The faunus girl took the slack in the bully's grip to free her ear. She stepped away from the guy but didn't move towards Torchwick.

"What're you looking at?" the bully asked, slowly rising from his seat.

He stood about the same height as Torchwick. His brown eyes looked into Torchwick's and screamed like the guy was ready to fight. Torchwick didn't even flinch; next to Cinder it was like he was starring an angry puppy down.

"Trust me Compensator," Torchwick said, gesturing to the guy's armor, "You know I'm here because you're being an ass."

"What was that?" the guy stepped in closer.

 _Oh Oum,_ Torchwick thought. _He's really close. I'm still thinking about how this is romance game. Oum, this is one step away from being a weird romantic encounter. Step back kid._

"Going to grab a girl's ears, honestly how petty," Torchwick said. "It's like grabbing her hair and puffing your chest out. Maybe the armor doesn't compensate enough."

"I'll kill you," the guy hissed.

"I'll avenge him," a new voice said.

The bully turned around to see the new person. Behind him was a girl in very fashionable clothes and a black beret. She stood half a head shorter than the bully but gave off a vive ten times more threatening than the bully. Behind her was a seven foot behemoth with a sword just as big slung across his back.

"Holy…" the bully said, tilting his head up to meet the gaze of the behemoth.

"You should consider the effects of your actions," the behemoth said.

"I'm… I'm sorry," the bully said.

"Don't apologize to him," the woman said. "Apologize to Velvet."

"Who?" the bully asked.

With that the woman growled and kicked the bully in the shin. He fell down grabbing his leg and gripping like a small child. Torchwick was again presented with an option:

 _-Intervene_

 _-Ignore_

Torchwick chose to ignore. He wanted to see the bully get beaten up; more than that he didn't want to go toe to toe with either of the new arrivals.

"You," the woman said. "Thanks for stepping in, but we got this."

"What's your name?" the behemoth asked.

"I'm Torchwick," he replied.

"I'm Yatsuhashi, and this is Coco," the behemoth said.

Torchwick looked to Coco who was holding the bully by the collar and shaking him back and forth. She was asking him rhetorical questions and shaking more violently when he tried to answer. Yatsuhashi began to try to calm her down.

"You should get to class," Yatsuhashi said. "Underclassmen lunch is about to end soon."

"Okay," Torchwick said, backing away from the scene.

The next hour was theoretical battle strategies followed by two hours of applied sparring with Professor Goodwitch. Torchwick held back against his partner, who'd been a buddy of the bully from lunch, because the poor guy was so slow for Torchwick. Even in this world a freshman was a freshman, and unlike Little Red they didn't have the same drive or finesse in a fight. After all the classes Torchwick returned to his room, exhausted.

"Why do people choose to do this," Torchwick said. "I didn't go to school and, I mean, I only turned into a criminal mastermind."

"You, a criminal mastermind?" Nora asked.

"How long have you been here?" Torchwick asked, rolling to face her.

"I was here when you walked in," Nora said. "You really are crazy. And not like me crazy, but the bad kind of crazy."

"I really don't care what a twerp thinks of me," Torchwick said.

"Why are you an ass only in front of us?" Nora asked.

"What?"

"This morning you were an asshole. But the rest of the day you're a good guy. Now you're an asshole again. Is it split personality or are you an all for show kind of guy?"

"I'm a sarcastic asshole all the tie sweetheart, you're just not paying attention."

"Really?"

"That bully, I was an ass to him."

"Yeah, but while saving Velvet. Although she didn't really need it."

"With a seven foot bodyguard like that, she doesn't need to fight Grimm."

"Anyway," Nora changed topics, "if you keep this up I'm not going to force myself to be kind to you. If this attitude hurts Pyrrha, or Oum save you Ren, I will break your legs."

"Oh no" Torchwick moaned sarcastically. "Oh yeah."

Torchwick pulled out the notebook from his pocket. After a full day it was a good idea to check the list of people he needed to seduce to end this game. He began to flip through the pages. First page was Pyrrha and it her full name, age, and 'difficult to seduce' which had her listed as medium. The next page was Nora who was marked as insane difficulty. The next page caught Torchwick off guard; it was Ren with a difficulty of insane.

"Hey, omnipresent thing," Torchwick called.

"Yes?" a voice resonated all around Torchwick.

"Why is a guy on the list of people for me to woo?"

"We're very accepting of the LGBTQ+ community. Our developer decided to include the option of gay romances in the game."

"So, you're saying I have to romance guys and girls?"

"Yes," the voice said.

"So what's my incentive to romance every character anyway?"

"True," the voice hesitated, "Every time you romance each character once I'll remove a thousand play throughs from your to do list."

"Seriously?" Torchwick asked.

"But I mean Every. Character. Successfully." The voice reiterated.

"Deal," Torchwick said. "It's not like I wanted to seduce an of these kids anyway."

Torchwick went back to looking through is notebook. Ruby, medium; Weiss, hard; Blake, hard; Yang, medium; Velvet, easy; Coco, medium; blank page; Yatsuhashi, medium; quite a few blank pages; Port…

"Omnipresence!" Torchwick said.

"Yes, him too," the voice cut Torchwick off.

"You sick bastard!"


	3. First Try

"Rise and shine Roman," Torchwick said to his reflection. "You have to seduce a minor today… That will never sound alight."

Roman moved by habit as he applied his eye liner. It took only a matter of moments to do his make-up. He then looked the work over to ensure it was satisfactory. Satisfied, he smiled and made finger guns at his reflection.

"Pow," he muttered, "I am hot stuff."

"Wow," someone said behind him, "That gave me second hand embarrassment."

Torchwick spun around to see Nora in the doorframe to the bathroom. He grabbed at his waist to ensure the towel he'd wrapped around hadn't fallen; it was there so nothing was exposed. She leaned again the post and looked at Torchwick with a smug look on her face. The dorm was empty behind her.

"Haven't you heard of knocking you twerp," Torchwick fumed.

"You're taking forever," Nora complained. "I still have to get ready. I'm not missing breakfast."

"Then get up earlier," Torchwick returned.

"It's Saturday," she said, moving into the bathroom. "I can get up anytime."

Torchwick put his eyeliner down, "Do you mind?"

Nora elbowed her way to the only mirror, "Not at all."

"Well I do," Torchwick said, elbowing back.

"Shame," Nora said, "I waited patiently for thirty five minutes. At this point you are going to share."

Torchwick scoffed as he left the bathroom. Nora closed the bathroom door behind him. He went to his dresser and grabbed todays outfit. Since it was the weekend he didn't have to wear his uniform. He laid out his black slacks and white coat. The outfit was the only reminder that he wasn't a student here, not really. A door behind Torchwick creaked open after he'd pulled his slacks on.

"Sorry," a girl said immediately.

"At this point you're trying to peep," Torchwick said, turning around.

He then realized that the bathroom door was still closed. Instead it had been Pyrrha coming through the front door that had seen him. She was blushing and averting her eyes as one hand wildly tried to find the door handle again.

"I didn't realize you were changing," Pyrrha said. "I swear I wouldn't walk in on you."

Torchwick was about to say something when the world greyed out. He was getting used to the options popping up, but he by no means enjoyed it.

 _-Look all you want. I'm not embarrassed._

 _-You're cute when you're flustered._

 _-I have pants on…_

"Wow," Torchwick said. "I somehow forget how dumb these options are. Also, the fact that one of these will make her like me more is just dumb. Let's see… 'You're cute when you're flustered.'"

The world continued and Pyrrha retorted, "I'm not flustered."

"You look pretty flustered to me," Torchwick said.

"Look," Pyrrha said, restoring her calm tone, "You can't change in here. Do it in the bathroom."

Torchwick realized he'd chosen the wrong answer. By the tone she'd taken, he assumed Pyrrha must've been upset by his attitude. Luckily he wasn't trying to win her over this time around. He'd set his sights on another girl. He was going to win the heart of Velvet Scarlatina.

His little notebook had difficulty ratings next to the various people he could seduce. Of all the entries he'd made yesterday she was the only one with an easy rating. He decided if he was going to learn the ropes it be best to start with a simple target. Like with pick pocketing you practice on the half deaf and blind before a huntsman.

"Alright," Torchwick said. "I'll change in the bathroom next time, so long as Nora stops walking in on me."

"She did?" Pyrrha said. "I'm sorry. She does that sometimes. She doesn't really have a lot of boundaries."

"Hey," Torchwick said, "You know where Velvet likes to hang out on weekends?"

"Um… why do you ask?" Pyrrha returned.

The world greyed out.

 _-I'm stalking her._

 _-I'm trying to seduce her._

 _-Reasons…_

"Wow… I thought the last options were bad," Torchwick said to himself. "Non e of them are wrong, but which one would have goody-goody actually help me? I guess, 'I'm trying to seduce her.'"

"What?" Pyrrha asked, astounded.

"What?!" Nora yelled, pushing the bathroom door open.

"You just met her," Pyrrha stammered. "Not even, you didn't even say anything to her yesterday."

"Are you a player?" Nora asked.

"Nora!" Pyrrha said, turning to her teammate. "Put on more than a towel! You're indecent!"

"Why Velvet?" Nora asked. "Do you like the innocent type? Are you a furry?"

"No," Torchwick said. "It's not like that. It's not a simple thing. I can't just chose who I fall for, but yesterday at lunch. I saved her and then, when she looked at me… my heart… just skipped a beat. My stomach felt funny; I've never felt love before, but this has to be the feeling."

"You fell in love… from eye contact?" Nora asked.

"Have you ever been in love," Torchwick defended. "It doesn't make sense. Sometimes you wait for it all your life. Other times, like destiny, you just meet them in the cafeteria on a completely normal day."

"Destiny…" Pyrrha muttered.

"Do you believe in Destiny?" Torchwick pushed Pyrrha.

She was quiet before saying, "She often goes into town with Coco on the weekend. You'll probably find her at Dusty Dress; it's Coco's favourite clothing store."

"Thanks," Torchwick said. "I want to see where this could go."

Torchwick left the dorm. It wasn't until he reached the end of the hall he let out a sigh of relief. It had been a long time since he lied like that. The whole destiny thing was an in the moment lie, and he was surprised how much it swayed Pyrrha. Thank Oum he'd gone with that over 'red strings of fate' or 'love at first sight' sort of joke.

"Dusty Dress," Torchwick said.

He stood outside a clothing store run by an old man who looked very similar to the one who owned the Dust store he'd robbed. The store was small and filled with various dresses, coats, jewelry, and hats. There was almost no rhyme or reason between the racks of clothing. However, Torchwick did find a couple things that actually looked good in his opinion.

"I'm not here to shop," Torchwick muttered to himself.

He looked around for the bunny. When he didn't see her he went to the store owner and asked. He told Torchwick that Velvet had been here not too long ago with the usual company. Torchwick left without another word.

He made his way down the street. He walked quickly and bumped into quite a few people along the way. He considered appearances, but then pushed them aside because this wasn't real life. If he made a scene everyone would forget eventually. Then he saw her up ahead; he more so saw a seven foot behemoth accompanied by some bunny ears.

"Hey," Torchwick called out. "Hey, Velvet."

She turned as Torchwick approached. She was with the two from yesterday and a third guy Torchwick didn't recognize. Now, standing in front of her and her trio of teammate/bodyguards he felt a lump form in his throat. He'd never asked a girl out like this. He'd done hook ups but it was only now dawning on him that he'd never been on a proper date.

"Uh…" Torchwick said.

"He, you're the guy from yesterday," the behemoth said. "The one who went to Velvet's aid. Uh… Towchwick, right?"

"The same," Torchwick said.

"Thanks," Velvet said. "You didn't need to intervene."

"I wasn't going to just stand by," Torchwick said. "When bullies pick on weak, it's disgraceful"

Torchwick felt sick just saying it. The irony of that statement, if only they knew. He'd done his fair share of things worse than bullying to those far weaker.

"Don't underestimate her," the fashionable one, Coco, said. "She isn't weak, but she doesn't want to fight things which aren't Grimm."

"So what are you doing here?" Velvet asked.

"I, uh…" Torchwick actually found himself wishing for one of the prompts, "Was curious if you were busy next weekend?"

There was silence. Velvet looked at him with surprised eyes. Coco, the behemoth, and the new guy all stared at Torchwick with a mix of messages. It must've been a few seconds, but the pressure around Torchwick made it feel like hours. He was surprised how stressful it was to ask someone out so bluntly.

"I'm free," Velvet said.

"You want to go on the town with me?" Torchwick was mentally beating himself for asking in such a cheesy way.

"Uh… sure," Velvet said blushing.

Next Saturday. Torchwick had a date on Saturday. It felt somewhat surreal. He felt a childish glee stir in the depths of his soul for the first time in years. He quickly squelched those feelings. This was Hell and he was playing a game. As soon as Velvet fell for him everything would reset and he'd be forgotten. That grim reminder was enough to silence his glee.

He got out of bed and readied for school. Despite plans he still had to go to school. Who knew how long it would take to win over Velvet even if it was an easy play through. Failing would get him kicked out and an automatic failure on this play.

Class went on complete unchanged. He hadn't told Pyrrha or Nora how things had gone on Saturday. He didn't want to be further interrogated by them or pressed further for why he wanted to date Velvet. He was sure that one, if not both of them, would see through his façade if pressed enough.

After Port's class Torchwick was on his way to Oobleck when he ran into Coco in the hallway. She was standing in the middle, feet firmly planted and arms crossed. Her eyes were hidden behind her shades. She moved only after seeing Torchwick approaching.

"With me," she said, grabbing his arm.

She led him to an empty hallway as whispers emanated from other students. Torchwick was getting irritated by Coco's behavior. Didn't she realize acting like this would spread rumors; rumors certain to impact his romance chance with Velvet. He suddenly focused on her as she pushed him against a wall and planted one hand firmly on the wall next to his head. She leaned in close and peered over her shades.

"Why are you asking Velvet out?" Coco asked.

"Huh?" Torchwick said. "You did all this, to ask me that?"

"Velvet is my teammate, and I'm her leader," Coco continued. "You better not be a skirt chaser who thinks they can get a quick score on her."

Torchwick felt a pressure start to build in the hallway. It triggered the primal fighting instincts Torchwick only called on in emergencies. This huntress was questioning him with the bloodlust one would expect from a killer. Torchwick calmed his nerves; for once he was glad to have experience with Cinder.

He batted her hand away from his head and said, "I'm no playboy. I'm a smooth talker, yes, but I don't want to merely seduce women. I want to love them. I feel like what I feel for Velvet is the beginning of love."

"Really?" Coco said, skeptical.

"Look me in the eyes and tell me I don't have a drive greater than a skirt chaser," Torchwick challenged.

Coco looked at Torchwick. He focused on his goal of winning over Velvet in order to get out of Hell. He projected every ounce of romance in his being in order to convince her not to intervene.

"I don't believe you," Coco said. "But, Velvet already accepted the date. Just know, I'll be watching. You make one slip up, you hurt her, and I'll see to it that you lose that pretty face of yours."

"So you admit my face is pretty," Torchwick said, throwing caution to the wind.

Coco didn't reply, merely walked away.

Torchwick stretched after Ooblecks class. Despite his face off with Coco he wasn't late. Now he had lunch. On his way down the hall he felt his arm get grabbed. He tried to fight off the grab, but it held surprisingly firm and guided him into another empty hallway. Torchwick wondered why the school had so many empty halls in between classes. He pushed the thought aside and focused on who'd pulled him aside. It was the boy from yesterday, his notebook said it was Fox.

"You better be serious about Velvet," the boy threatened.

Torchwick went to reply, but the guy already started walking away. Torchwick just ignored it and went on to the cafeteria. Waiting for him outside was the behemoth. He wasn't pulled aside this time, but the behemoth did wave Torchwick over.

"I do hope you are serious about Velvet," the behemoth told him.

"I am," Torchwick returned, gritting his teeth.

"I won't fault you for falling out of a crush like my teammates," the behemoth said. "But you better treat Velvet well if this goes somewhere."

The behemoth patted Torchwick's shoulder gently and continued into the cafeteria. Torchwick followed, got his food, and sat with the rest of his team and team RWBY.

"If it isn't the playboy," Yang said as he sat down. "Already going after Velvet huh? Like the older women?"

"So what did Coco want earlier?" Pyrrha asked.

"Her team thinks along the same line as Yang," Torchwick said. "Not one of them trusts that I'm serious about Velvet."

"To be fair, you just got here," Nora pointed out.

"It is really fast," Ruby agreed.

"Young love works like that, right?" Torchwick asked.

"You sound like you aren't our age," Weiss observed.

"I come from a complex background, I'm very mature for my- our age," Torchwick corrected.

There was a collective sigh from the table.

"What?" Torchwick said.

"Nothing," Ren said. "So, what are your date plans?"

"I…uh," Torchwick realized he'd made no such plans.

"Oooh, I wanna hear this," Yang perked up.

Torchwick was a confused. Was he supposed to plan the date in a dating simulation? He assumed the mini-game he'd been told about would count as the date. If he was wrong he was in for a terrible Saturday.

"You don't have a plan, do you?" Blake asked.

"I uh, not… yet," Torchwick said. "I'll have one by Saturday though."

"Velvet sure is a lucky girl," Weiss said, finishing her meal.

The days flew by and before Torchwick knew what to do it was already Saturday. He'd thought over so many plans but none seemed good. They were either too childish or something criminal he used to do with Neo. He was pretty sure Velvet would not be up to robbing a chain of stores.

He went to the meet up place early. He had decided to wear his usual casual clothes; they made him the most comfortable. Despite being ten minutes early Velvet was already there. She wore a brown dress and sun hat that had holes for her ears to peeks through. She had a camera and was taking photos of the weapon shop across the street by the looks of things. She put her camera away as Torchwick approached.

"Sorry I'm so early," Velvet said. "I was doing something that ended early and didn't want to head back to the dorm."

"It's fine," Torchwick said.

Torchwick caught something out of the corner of his eye. He double checked and felt himself tense up. Sitting behind a newspaper at a nearby coffee shop was Coco. She was peering menacingly over the paper, but pulled it up when she noticed Torchwick looking around. This went beyond over protective to creepy.

"Are you ready?" Velvet asked.

"Yeah," Torchwick said.

Suddenly green beams shot up from the ground around the two of them. They formed a circle and everything in town began to fade into darkness. He felt himself standing on something even as the floor faded from view. It felt like he was falling and flying at the same time. These sudden changes didn't even phase Velvet.

"Welcome to Grimm-emon snap," the tutorial voice said. "Is this your first time playing?"

Torchwick turned around and saw a screen had appeared. It had simple text the read "Grimm-emon Snap." Torchwick was only sort of familiar with Grimm-emon. It was a game that had players catch, tame, and fight with fake Grimm. He had no idea what in Remnant Grimm-emon Snap was, but it must've been some spin off.

"It is my first time," Torchwick said.

"Then allow me to explain the rules," the voice said. "You will be given a camera and moved along a predefined path. Along the way you will see Grimm-emon. Don't worry, they won't attack. Your goal is to take the most valuable pictures of these Grimm-emon. Whoever has the higher score at the end is the winner. Best of three rounds. Understood?"

"Sure, enough," Torchwick replied.

Torchwick found himself in Forever Fall forest. He wasn't walking but found himself slowly moving along the path. In the corner of his vision was a small film roll with a number 60 next to it. In his hands was a small camera. Velvet was nowhere to been seen.

"A date where we don't even see one another," Torchwick said. "The hell is the appeal of dating sims?"

Torchwick saw a Grimm looking something off the side of the track. He pulled the camera up and snapped a shot. He didn't recognize any of these Grimm. A couple looked like Beowolves, but he was certain they weren't. On top of that he was sure he saw just a regular old cow among the Grimm-emon. He took its picture hoping it was some sort of legendary. The track lasted about five minutes before he suddenly teleported back into the room from earlier.

"Time to tally first round scores," the voice said.

Velvet was kicking her foot back and forth on the ground as their pictures were scrolled through. One by one the pictures were given point values and added to a total score. Initially the scores were similar, with pictures worth a couple hundred points apiece. Then out of nowhere Velvet's score started skyrocketing with shots worth thousands of points. Torchwick audibly gasped when his picture of the cow was given 50 points and Velvet had another picture of the same cow worth 500 points.

"How?" Torchwick asked.

"Yours was too blurry and you didn't get the cowsprice's eyes," Velvet explained.

"The final scores for the first round: 3,500 points for Velvet and 1,600 points for Roman," the tutorial voice announced. "The first round goes to Velvet. Beginning round two."

And like that Torchwick found himself on a new track which must've been some road between kingdoms. He steeled himself and started snapping pictures. He had no idea what he was doing, but he wasn't about to lose the first mini-game without giving it his all. He became competitive when he got upstaged and the person didn't brag about it. Some people needed to learn to grow and display their ego.

Torchwick used all 60 shots on the second track. The game started tallying their scores. Torchwick's brow furrowed as Velvet's score visibly changed between the first round and second round. Her shots were consistently similar in score to his own.

"You started pulling your punches," Torchwick said.

"No, I've never been good on Route 86 before," Velvet said. "I try to take to many legendary shots and mess them up."

"Don't do it again," Torchwick said. "I don't need your pity."

"Final score for round two: 1,500 points for Velvet and 1,700 points for Roman. Roman wins the second round. Beginning round 3."

Torchwick gasped at the setting for the third round. It was Salem's base of operation. He'd only heard about it from Cinder, but there was no mistaking the description and what he was witnessing. It was the fields in which Grimm were born. How the Hell did they know about this? Who behind Grimm-emon had this sort of association to Salem?

He pushed those thoughts aside and started snapping pictures. This round was do or die for this date anyway, and he wasn't keen on loosing. About halfway through the route he realized he was going to lose unless Velvet wasn't trying again. Then he saw something on the horizon that looked interesting. He zoomed in as far as he could on his camera. It looked like something on a horse with spindly arms dragging behind. He didn't get much detail, but decided to snap the picture anyway. It wasn't much, but it might make his margin of failure smaller.

"Time to tally the scores of the final round," the tutorial voice said when the route ended.

The scores started to roll in. Once more Velvet outpaced him with shots worth at least twice those he took. Torchwick hung his head and Velvet patted his back.

"You really tried," Velvet consoled.

"I don't need your pity," Torchwick said.

There was a bang. Torchwick looked up to see his photo. It was outlined in gold. It had fancy text underneath it that read "Shiny Nuckelavee." He didn't know what that meant but the photo was worth… 10,000 points. It leapt him bounds beyond Velvet's score.

"Shiny…" Velvet muttered. "I got the Nuckelavee, but shiny… those only occur one in about every eight thousand instances. To get the legendary shot, with the shiny modifier… That's awesome!"

"So… I won," Torchwick asked.

"Final scores: 3,700 points for Velvet and 11,500 points for Roman. Roman wins the date."

Torchwick's vision faded. A picture of Velvet appeared in front of him. Words and numbers began to scroll across his vision. He realized he was getting rated on the date. The scores came from effort, appearance, attitude, dialogue, timing, and what must have been a dozen other aspects of the date. The final score he got on the date was 1,050. A progress bar around the picture of Velvet filled with the score.

Torchwick let out a exasperated sigh. His score hardly filled a fourth of the bar. He'd have to do this four more times to win her over. Then he got more messages. He'd apparently done some things that earned him bonus points: "Winning the date: +250" and "Shiny Grimm-emon: +3,000" which together filled up the bar completely. He'd managed to win Velvet in a single date by sheer luck.

The screen asked for him to continue. He starred for a second before accepting. He found himself back where the date had begun. Velvet stood really close to him, blushing and avoiding direct eye contact.

"I had a lot of fun today," she said.

"Uh, so did I," Torchwick managed.

She was really close. She was inching even closer as she spoke. Her ears were perked up and her hands fidgeted with her bag. This was what happened when she fell for him? Torchwick had no idea what to do or where to look. Then the world greyed out.

 _-Go for the kiss_

 _-Pat her head_

 _-Do nothing_

"Oh fuck," Torchwick said. "Which do I do? Is filling the bar all the way enough to kiss her? Should I wait? She seems pretty timid. I don't want to push this and trip on the home stretch. How do you win a dating sim? Is this an ending? Oh shit, should I do nothing? No. I have to do something. Kiss? She's a child. This is wrong, oh boy. I'm too damn flustered about this. Fuck it. Go big or go home."

Torchwick leaned in slowly. He gently turned Velvet's head with his hand so she was facing him. Her eyes looked at his with surprise and her face turned red. Torchwick's lips met hers and she didn't pull away. Her lips were softer than he'd been expecting. He was too focused on throwing up; he was at least ten years older than this girl.

"OOOOH NO YOU DON'T!" Someone was screaming.

Torchwick felt someone kick him in the ribs which broke him away from this kiss. He went sprawling across the ground. Velvet was a little slow to notice Torchwick had left and opened her eyes suddenly when she realized he'd vanished. Standing next to her, breathing heavily, was Coco.

"No," Coco scolded. "Not on the first date. No. I knew you were a playboy."

"Coco stop," Velvet pleaded, her face flushing even redder. "It's not like that."

"Velvet you naïve slut," Coco said. "You met him not ten days ago. You've seen him what? Three times. Do you even know his eye color?"

"Why does that matter?" Velvet asked.

"I know you," Coco said. "You've fallen for this guy. You don't know anything about him. Chill your tits, and save kissing for at least the third date or after six shots of tequila."

"You want me to date him more first, fine," Velvet accused. "Roman, are you free next weekend? I'd love to go on another date."

Coco gasped. Torchwick rolled to a sitting position on the ground. He was using all his mental focus to not berate Coco for kicking him. It was also incredibly taxing to not respond sarcastically like he always did. He had to seal the deal and finish this lucky playthrough right here and now.

"I'd love to, Velvet," Torchwick said.

The world vanished. Giant gold letters reading "Congratulations" appeared in front of him. Torchwick rolled onto his back, the world following his line of sight. He noticed beneath the congratulations it asked "Play again?" with yes as the only option.

"Hahaha," Torchwick laughed, "First try. I'm a natural."

"You're lucky," the omnipresent voice said.

"You're just mad," Torchwick said.

"I can up the difficulty."

"Please don't," Torchwick asked. "That was enough suffering."

"Fine, but only since you asked politely."


	4. Caffeine

How many times had Torchwick failed? Sixteen times? Seventeen? The omnipresent voice had been right; it was just a fluke he'd succeeded his first play through. This game was leagues more complicated than he'd realized. The men and women were infinitely complex with wants that actually changed depending on their mood and romantic progression. Torchwick felt like he was actually trying to win over real people and not a series of ones and zeroes. It infuriated him.

He'd tried to romance Velvet again for an ego boost, but down the path she broke up with him for being overly doting and protective. He'd tried the Blondie but she wouldn't even give him a first date. One of his attempts to romance Professor Goodwitch ended in an expulsion on the spot. This game was supposed to be easier than it was turning out.

After about the tenth failure he decided to do a few run throughs and take notes. Simply winging things just wasn't producing results and he was not about to spend a millennia and day on this game if he didn't have to. He played two games to the end of the year he had to romance one person. He hadn't come close to any successful romance in that time, but he had learned valuable tidbits and hints in so doing.

What he'd learned from all his notes was each character had a go to aspect of their personality; it was a place they'd always be, a food they'd always enjoy, or an activity they'd never turn down. In practice, at least, that was how it seemed to play out. Aspects like Ruby never turning down a cookie even if she was on deaths door levels of sick. He also learned that Weiss was drawn to gossip like a moth to flame, and if played correctly would spill information on her teammates. By far the most important thing Torchwick had learned was the Ren existed as a wingman character. He would give Torchwick hints, pointers, and advice on how to approach the character who had the highest romance progression.

Torchwick had also uncovered something that countered all the good he'd learned; the game was not static. Even if he responded to the same way to the same questions it didn't result in a similar situation. The dialogue he chose when meeting his teammates was the same each time, but how he said the options seemed to affect how his teammates perceived him. One time he tried all sarcastic answers and Nora became more sarcastic back whereas one time he was monotone with all the responses and Ren became more buddy-buddy with him.

It was all so infuriating. No game had this level of branching in story options. It would be impossible to memorize the fastest way to romance a given character if the level of interaction was so complex. Torchwick was coming to a terrible realization: he'd have to actually try each time he played.

"Mr. Torchwick, would you care to stop day dreaming and answer?" Oobleck announced loudly.

Torchwick snapped back to reality. He was in Oobleck's class "listening" to him drone on about something. He hadn't been paying attention in the slightest and had no idea what to answer. The world greyed out, and for once he was glad to have guided options for the question.

 _-2008_

 _-Mountain Glenn_

 _-CCT_

 _-Cinder_

"What?" Torchwick spewed. "These aren't related at all. Why is Cinder even an option?"

"An option of what?" Oobleck asked.

Torchwick had done it again. He'd said an answer while questioning why it was an option. He was never going to stop doing that.

"Who is Cinder, Mr. Torchwick? She certainly isn't the answer to my question," Oobleck continued.

"I… uh… wasn't paying attention," Torchwick said.

"Then let me repeat my question to the class: what is the name of the failed Vale expansion to the South East?"

"Mountain Glenn," Pyrrha answered.

"Correct Miss Nikos," Oobleck praised. "Class is wrapping up, so please study that for your exam next Friday."

After Oobleck's class was combat practice. Torchwick never paid attention during combat practice because he'd seen more real fights in a week than these kids had seen in their lives. Today was Thursday so there was going to be sparring matches tomorrow. That meant today was reviewing combat theories covered this week.

"Who do you think you're gonna be paired against tomorrow?" Nora asked Pyrrha.

"I don't know," Pyrrha said.

"Professor Glynda needs to match you against more than one opponent for a fair match," Ren pointed out.

"I wouldn't go that far," Pyrrha said.

"You're to humble," Torchwick said. "Your semblance gives you a massive advantage in one on one. The purpose of class is to improve ourselves, but if you aren't challenged you aren't improving."

"I suppose," Pyrrha said.

"Speaking of semblance," Nora began, "you haven't shown yours yet, Torchwick. Is it a secret?"

"I don't need it for these matches," Torchwick said. "I also don't use it in regular combat like Pyrrha so it just never comes out."

"Are you underestimating us?" Nora asked.

"You don't use your semblance in these fights either," Torchwick pointed out. "Are you underestimating us?"

The four of them took their seat in class. They sat in the second row with team RWBY. Their class was a hybrid of first years and volunteer second years. The second years volunteered to repeat the course to spar against incoming freshman to hone their own skills and bolster those of their juniors. It was an interesting approach in Torchwick's opinion, but he would never be such a volunteer.

"He's got you there Nora," Ren agreed.

"Hey Ren," Torchwick said, "I've never seen your semblance either. Is it not a combat semblance?"

"It's – " Ren began.

"Settle down," Glynda started class on the dot. "As you know we have sparring matches set for Friday. However, this week I'm going to do something different. This week you'll be fighting in teams of two with randomized partners outside your typical team.

"The purpose of this exercise is to build quick communication on the battle field. You won't always know who you're going to end up working with on missions so you need to be able to adapt on the fly. As Huntsmen and Huntresses you will probably know the skills and abilities of fellow Huntsmen and Huntresses, but not have a lot of experience working with those people. Similar to this classroom you know the styles and abilities of your classmates, but little experience in tag team efforts. To keep you underprepared I will announce the teams tomorrow right before the match."

"This'll be good," Torchwick muttered, glancing around at possible teammates.

"The sparring will also be a bracket system in which the top four teams get extra credit; first place receiving a little more than the next three. Since class is only so long we will only hold half the matches tomorrow and the rest will be on Monday. This will give each surviving team some time to hone their cooperation over the weekend."

Torchwick suddenly realized why this tournament was happening. Grades meant nothing; the real incentive was winning the first match. Over the weekend team building meet-ups would be an implicit date and a chance for him to build up his rapport with someone. If he played it right he might even get a proper date out of things.

He double checked his notebook. This time around he'd made some headway with Weiss, Yang, and Pyrrha. Since he wasn't going to be paired with a current teammate his best hope for tomorrow's matchup was Weiss or Yang. He could win a preliminary fight with either of them as his partner which would secure a weekend date. He smirked as he put his notebook away.

Before Torchwick knew it, it was next class. He'd refreshed himself on how Yang and Weiss fought; it was all he could do for today's match. His only concern was his first matchup would be against Pyrrha and her partner. It didn't matter who he was working with, against the Invincible Girl they would lose.

"Is everyone ready for today's sparring tournament?" Glynda asked.

The class gave a hearty cheer. They were all decked out in their combat outfits. Torchwick saw Yang's legs shifting in place as she cracked her knuckles in anticipation. He wasn't going to lie; he was pretty pumped for the fights too. Sparring was the greatest stress relief he could get in this Hell-scape.

"Our first match will be Pyrrha and Cardin," Glynda announced, "against Velvet and Weiss."

Unfortunate, Torchwick thought to himself. Pyrrha was about to carry Cardin to some extra credit. It was also unfortunate because now Torchwick could only gain if paired with Yang; any other teammate would be a fresh start relationship. He'd rather avoid starting from scratch this play through.

The match was over almost as soon as it began. Pyrrha rushed Velvet and had her aura depleted in a matter of moments. Torchwick wondered why Velvet never used the box she always carried on her back, but guessed it must be some sort of support weapon instead of an offense thing. With Velvet gone Weiss couldn't hold out in a two on one very long.

"That's the match," Glynda announced. "Pyrrha and Cardin are moving on to Monday's rounds. Our next match will be Blake and Ren versus Coco and Torchwick."

Coco? The girl that used the minigun briefcase? Torchwick grit his teeth as he made his way to the sparring arena. Not only did he have little to progress romancing her he wasn't sure their fighting styles would sync very well. She was a high damage range fighter and he was a close quarters support. They were also going up against a formidable duo who both used a mix of close and ranged combat, and on top of that their actual form was complimentary. It was like the docks all over again, but fewer monkeys.

Torchwick took his position next to Coco on their side of the arena. He looked across at Blake. He had a fair record with her of one win and one loss. He scanned to Ren who he'd only fought in team practice.

"Try to pin those two into a corner," Coco muttered.

"It's a circular arena, there are no corners," Torchwick replied. "Just shoot even if you might hit me."

"Big noble sacrifice type?"

"No, I'm good at pulling out before things get bad."

"Phrasing," Coco said.

"You're a child," Torchwick returned.

"But I'm your senior."

"3…" Glynda began counting down. "2… 1… Begin."

Coco's gun became a mini-gun immediately and began laying down a hail of bullets. Torchwick fired his cane to Ren's left to force his retreat to the right. Blake and Ren both took the bait and rolled to the right to avoid the incoming attack. Coco spun in place to chase the two of them with her mini-gun. Torchwick ran behind the bullets and closed the distance between himself and his opponents.

"Blake, Up," Ren shouted.

Blake spun on her heel and leapt onto Ren's Shoulders. She pounced into the air over the bullet storm. Once over the bullets she created a shadow clone and used it as a springboard midair. She was headed directly for Coco. Torchwick had to hand it to them for such a quick plan; if Coco shifted her aim to Blake it opened her up to Ren, but if she did nothing Blake would hit her.

"Coco duck," Torchwick yelled.

Coco interrupted her fire and took a knee to avoid whatever was coming. Blake glanced over her shoulder to see what was coming. Torchwick had raised his cane and was aiming at Blake's path. She created a clone and pushed off it to change her direction. Torchwick didn't fire, he hadn't planned to. He instead swung his cane to block Ren's attack.

"Gotcha," Torchwick said smugly to Ren.

It was now two one on one fights. He was at a disadvantage against Ren. He could easily defend against any of Ren's attacks but any attempt he made to strike back would leave him too vulnerable. Ren was faster and more nimble; darting around into Torchwick's blind spot and slashing with his gun or firing a few rounds. He was going to tire out before Ren at this rate.

"Secret technique," Torchwick muttered.

He'd muttered it just loud enough for Ren to hear. Ren hesitated and shifted his stance to a more defensive posture. It was subtle and only a couple second window for Torchwick to act, but it was exactly what he needed. Torchwick spun hard on his right foot.

"Run away," Torchwick announced.

Ren didn't react. Torchwick was half-sprinting away from the fight. On top of that he wasn't even running towards Blake and Coco. He was full on running from everything.

"Oh Hell no," Coco yelled. "Torchwick I will kick your ass!"

"Only if you can catch me," Torchwick returned.

Coco began to sprint after her teammate. Blake and Ren didn't react to the enemy implosion they were witnessing. Torchwick was running along the edge of the arena with Coco hot on his heels.

"How can you keep up in those demon boots?" Torchwick asked over his shoulder.

"Practice and spite," she yelled. "Get your mascara ass over here!"

Torchwick turned and aimed his cane at Coco. Her eyes narrowed and he winked. He subtly made his free hand point down. Coco smirked as she understood his plan.

"Sweep the legs," She yelled, turning her sprint into a slide tackle.

Torchwick fired his cane. He then took a step forward, passing right over the would be slide tackle, and spun his cane around. He caught the shot with e handle of his cane and swung it towards the dumbstruck Blake and Ren. He'd turned his shot into an explosive arc of energy. Since they were at the edge of the arena it was going to pass over every inch of fighting space.

"What?" Blake said, leaping into the air.

Coco was on one knee and holding her mini-gun tightly. She open fired at Blake who was able to easily dodge. Ren, who had also jumped over the arc of energy, was less mobile and took a dozen shots head on. His aura dropped into the red and was eliminated from the match. As Blake landed she was greeted by Torchwick who swung his cane like a bat and knocked her out of the arena.

"That's the match," Glynda announced. "The winning team is Coco and Torchwick."

"That plan was risky," Coco said.

The two of them had met up the next day at her favorite coffee shop to plan for the rest of the tournament. They sat across from one another at a table on the patio. The sun soft behind some cloud cover.

"I'm just glad you caught on," Torchwick said.

"When someone screams run, I assume he has a plan working behind the scenes," Coco said. "I was right in assuming you had at least that level of intelligence."

"Alright," Torchwick shifted the tone, "We need a plan against our opponents."

"Right," Coco said, "There are seven other teams. We need a plan for each."

"There's Cardin and Pyrrha," Torchwick said.

"They're probably worst case scenario. Cardin is easy, but Pyrrha is someone I'd rather put off fighting as long as possible. You're on her team, what are her weaknesses?"

"None, really," Torchwick admitted. "She's very good at analyzing a fight and handling it in the most efficient way possible. She can handle sudden situations on the fly and could probably take down the both of us solo. If anything, Cardin is a hindrance to her."

"That's not good for us."

"It's actually perfect. Despite how much she hates Cardin, he is her forced teammate. It isn't in her nature to attack a teammate. I say we get into close quarters with Cardin and attack Pyrrha from there. She'll be limited in counter attacks because of how close we are to Cardin and he's close range style is easy enough to dodge."

"That's ruthless, but I like it."

"Then we have Ruby and Nora," Torchwick said.

"We focus Nora first," Coco said. "She's a powerhouse that could take us out in a hit or two. We take her down as fast as possible. Ruby's speed will lose some edge in a two on one."

"It doesn't hold up in a one on one sometimes," Torchwick said. "Dove and Yang, probably same approach; take out the powerhouse and go from there."

"Dove won't be a problem," Coco agreed.

The two of them talked more in detail about strategy and plans against specific opponents. They talked about key words to yell for combo attacks. Slowly, Torchwick worked the conversation from battle to personal life. He was going to turn this tactics meeting into a date if it killed him.

Suddenly the world around Torchwick became saturated. It took him by surprise, but he realized he'd turned things into a date and the world was becoming a date. A smile crept onto his face as he congratulated himself. He at the table to see Coco had pulled out a deck of cards.

"We're going to play a little game," Coco said with a smirk. "How are you at poker?"

A prompt appeared in front of Torchwick. It asked if he knew how to play poker.

 _-Yes_

 _-No_

"Yes," Torchwick replied. "I've played more poker in a day than you've played in your life."

"We'll see about that," Coco returned, and started dealing out hands.

Chips materialized beside Torchwick. He had ten 100 tokens, eight 250 tokens, and four 500 tokens which totaled five thousand points to gamble. He assumed this would translate into his affection points if he won and then he'd get some sort of bonus points for how he played.

He picked up the cards he'd been dealt. Three kings, a three, and an eight. He made no reaction to this hand. He raised the pot by a hundred points which Coco met. He shifted the cards and eventually discarded the three and eight. He got a two and a ten in return. Again, he maintained his poker face and hoped Coco hadn't gotten something better.

"Alright, reveal," Coco said, laying down a full house.

"Shit," Torchwick said, showing his three of a kind.

"My win," Coco said, taking the pot.

She passed the cards to Torchwick and he shuffled and dealt this round. He got four spades all around the deck and a diamond, but among the spades was a five, six, and seven with the diamond being an eight. He raised the pot by a hundred again and gambled on the flush. He got lucky and drew his fifth spade. Coco discarded three cards and matched his bet.

"Reveal," Torchwick said.

Coco had two pair which was easily beaten by his flush. The game continued in a back and forth manner for some time but was slowly turning against him. Torchwick began to notice something as he played. Coco won almost every hand when she was the dealer but only a little under half the hands when he was dealing. Then he saw it.

Coco dealt herself a card just under the top card. It was done so fast he'd almost missed it. He pushed his chair out grabbed her hand before she could react.

"What?" Coco asked.

"What do you think you're doing?" Torchwick asked.

He grabbed her cards and flipped them over. She had four kings. Torchwick narrowed his eyes at her. He as beginning to kick himself for not taking the tutorial or he might've noticed earlier.

"Second Dealing," Torchwick said.

Coco's eyes widened. And she put the deck of cards down. A smile began to spread across her face.

"You were cheating," Torchwick said.

Second dealing is a trick for expert gamblers, but only works if you're the dealer. Coco had memorized the order of the cards, either by intuition or she'd been counting them this whole time. As the dealer, with the order of the deck memorized, she could determine her hand before it was even dealt. Second dealing was where she pulled the card just under the top card because it would lead to a more favorable hand.

"You caught me," Coco said.

"I'd have noticed sooner if I knew cheating was allowed," Torchwick said.

"Looks like I'll have to take you more seriously next time," Coco admitted. "Since you caught me cheating the game is your win. Next time, I won't get caught."

The world faded to a score board. He earned a hundred points for winning and then earned a series of bonus points for his best hands in the game. He then got an additional hundred points for catching Coco cheating. His final score was two hundred and forty six. That number began to fill the progress meter for Coco. It came out to about a sixth full. By estimation Torchwick realized he needed around one thousand five hundred points to get a kiss from Coco. With her poker skill this might pose a serious challenge.

The following months were about as back and forth as the games of poker. His wins were nearly matched by his loses. Just when he'd start to go on a series of victories he'd get shut down by a comeback from Coco. Unfortunately, losing meant his romance progress was also set back.

The games evolved into high stakes matches with both sides cheating so cleanly the other player couldn't catch it. About the fifth date an independent card dealer was provided for the mini-game to prevent cheating by the dealer. After the eleventh date whoever designed the mini-game must have had enough. A new rule was added that you may only cheat on one hand per game. After that the dates began to return to the psychological warfare that is Poker and less so the cheating warfare.

Torchwick had also learned something else from this slow romance progression. Coco had started acting more romantic towards him. The higher his romance progress the more she behaved like it. When he messed up she became more distant. The game felt so realistic he often time forgot none of the people around him were real. He mulled this all over some lunch.

"Hey Roman," Coco said, taking a seat next to him.

"Hello," he replied.

"I was having a party this evening if you're free," she said.

"Yeah," Torchwick said. "When is it?"

"It starts at seven in my team dorm," Coco said. "The guest list exclusive, don't tell anyone."

"See you then," Torchwick.

The party was small scale since it was confined to a single dorm. All of team CFVY was there and a handful of others. There was Torchwick, Yang, Blake, Weiss, Nora, and Ren. Coco, Yang, and Nora were drinking some of the alcohol Coco had snuck in. The group was playing Super Smash Hunters and alternating controllers among the losers. Torchwick prayed this wasn't anyone's mini-game because he was absolutely terrible.

After about two hours of gaming it was getting really late and the games shifted away from the console to other games. The played a few rounds of never have I ever. Torchwick was eliminated first or second in all four games they played; it couldn't be helped since he was an actual adult. By the end of the fourth game those drinking were beginning to be obviously drunk.

"Hey," Coco began, "Let's play some cards."

Torchwick's ears perked up. Cards might mean poker, and that meant he might make more romance progress.

"What'll we play?" Blake asked.

"Poker," Coco managed.

Torchwick smiled at his luck. In her drunken state he could easily pull a victory and max out her romance bar. Then he'd be able to secure a first kiss at his leisure.

"Poker is too boring," Yang said.

"Why?" Ren asked. "I think it has a lot of depth and strategy."

"We don't have anything to bet," Yang countered.

"I got an idea," Nora added with a hiccup. "Our clothes."

The room fell silent and everyone looked at Nora. She was propped up against Ren and was making a sultry smile at everyone.

"Nora, are you suggesting strip poker?" Weiss asked.

"Yheap," Nora said.

"Nora, you're drunk," Ren said. "We can't play strip poker."

"I'm still good," Nora argued. "Look, I can still do one handed push ups."

Nora pushed off Ren and immediately went to doing pushup with one arm behind her back. Torchwick was actually surprised at how well she was managing the pushups. Torchwick didn't have the strength to that in any state of mind.

"Nora, you only do that when you're drunk," Ren said, "or at the gym. Since this isn't the gym, you're drunk."

"Coco," Yatsuhashi began, "is this why you did not invite Ruby to the party?"

"What?" Coco countered.

"You planned this," Fox said.

"No… maybe a little," Coco admitted. "I wasn't expecting strip poker, but… eh… maybe some more adult themes."

"I thought it was because you were sneaking in alcohol," Velvet said. "That's also why I thought you didn't invite Pyrrha."

"Pyrrha wouldn't paly strip poker," Yang said. "And none of you… boys are going to see Ruby like that."

"I'm not going to play strip poker," Fox said.

"I will," came a sober voice.

The group turned to see Blake had been the one to speak up. Torchwick's inner monologue devolved into nothing but screaming. He didn't like where this was going. He may be in a young adult's body for the story, but he had practically a decade on everyone here. He wasn't really into kissing these girls and boys, but if it meant escaping hell he'd do it. Playing strip poker? That was crossing a lot of his lines.

"I'll play," Yang agreed.

"Count me in," Nora said.

Ren sighed before saying, "Why not."

Torchwick was internally panicking. Even the level headed Ren was joining in. He had no idea what to do. Saying no might be a big set-back with Coco. He only had so much time to win the game, and a big enough set-back would screw his chances. He also had no idea if this was how Coco's story would go each time and saying no now would only delay the inevitable.

"I'll play," Yatsuhashi said.

"Seriously?" Fox said.

"I cannot go anywhere for this I my dorm too," Yatsuhashi explained. "I should at least play if I'm going to stay and watch."

"Ergh," Fox moaned, "I'll play."

"I guess I'll play too," Velvet said.

"This is childish," Weiss said.

"Is the heiress too above playing?" Yang prodded.

"I thought she'd win hands down," Coco added. "I guess this Schnee doesn't take risks."

"How dare you," Weiss began.

"Chicken," Yang said.

"I am not," Weiss protested.

"Prove it," Nora finished.

"I… you…" Weiss said.

"Weiss, you don't have to play," Yatsuhashi said.

Wrong move big guy. Torchwick knew Yatsuhashi was trying to be nice and avoid pressuring Weiss. However, Torchwick guessed it was about to have the opposite effect. Weiss was to prideful to walk away with an out given to her.

"I'll play," Weiss concluded. "I'll show you all."

"Torchwick?" Yang asked.

He clenched his fists and said, "Sure, but with ground rules."

"Of course," Coco said, going to her desk drawer and pulling out a deck of cards.

"First," Torchwick began.

"Why do you make the rules?" Weiss interrupted.

"You can add any if I miss something," Torchwick offered.

Weiss nodded.

"First, we all need to have the same number of layers," Torchwick said. "It wouldn't be fair for one person to have fewer chips than another at the start."

"Seems fair," Ren agreed. "How do we divide it up?"

"We count how much we're wearing and pass our excess to someone else or just discard it," Blake proposed.

"Do we count shoes and socks?" Velvet asked.

"Hmm," Coco began.

"No," Fox said. "Not individually. Both shoes are one things and socks should be another."

"Kay," Yang affirmed.

"What about underwear?" Nora asked.

"That was my second rule," Torchwick said. "Not everyone is as… confident as you are Nora. We play to underwear and no further."

"I second that one," Weiss affirmed immediately.

"Agreed," Yatsuhashi said.

Everyone counted how much they had. Torchwick had the most at eight pieces; his jacket, scarf, shirt, pants, shoes, socks, gloves, and hat. Weiss was in last with three in her dress, shoes, and socks. The clothes were redistributed so each player had five. The now mix and matched players waited for further rules.

"Third rule," Torchwick continued, "how the loser is decided. Anyone who doesn't fold when hands are revealed has to lose a piece of clothing. If you fold you are exempt that round, but if you fold three times in a row you automatically have to strip."

Torchwick's stomach lurched as he recited the rules from the last time he played strip poker. It had been five years ago in a bar with some old colleagues. The difference was everyone there was about the same age and they were all adults. Here the setting was just wrong in Torchwick's mind. However, if he left it up to the kids the rules would be either impossible to follow or unfair.

"So a bad hand isn't a death sentence," Fox explained, "I like it. I agree."

There were nods of approval.

"Fourth," Torchwick said, "You may withdraw from the game at any time. Anything lost during the game cannot be collected until the end."

"What do you mean?" Yang asked.

"If you run out of clothes," Torchwick explained. "You're out. If you decide you don't want to play anymore, you're out. Once you are out, you cannot take back your clothes until only one person wins the whole game."

"I like it," Yang said once she understood.

"That's all the rules I can think of," Torchwick said.

"What do we do with the bet clothes?" Nora asked.

"How about the winner gets to wear them?" Ren suggested. "Giving them more to bet in coming hands."

"And more options to fold," Weiss added.

There was more approval.

"Fifth," Torchwick continued, "Since we only have five 'chips' each there won't be any ante. We only raise or fold."

"I'll deal," Coco said, reaching for the deck.

"Not so fast," Torchwick cut off, "You have a knack for sly dealing moves. I vote Ren or Fox deal."

"I'll do it," Ren offered. "Also, since there are ten of us we should probably play Texas Hold Em instead of Poker."

"Why?" Nora asked.

"If we played poker we'd each need five cards and that would leave the deck with two. If we played Texas Hold Em we'd each get two cards and the center five."

"That sounds good," Yatsuhashi agreed. "The winning hands are the same anyway."

"It would also making betting more interesting," Fox added.

"Bring it on," Yang said.

Ren dealt everyone their two cards and rolled out the first three center cards.

"I don't remember exactly how to play," Blake said. "We get our two cards and I thought Ren would play all five of the center cards."

"Not when betting," Torchwick said. "We get our cards and then the center three. Then we can raise and bluff. Then Ren will play another center card, we bet some more. Then he plays the last card and we reveal our hands. We can't bet or fold once the last center card is revealed."

"And the center cards go for everyone, right?" Weiss asked.

"Yeah," Fox affirmed.

Torchwick checked his hand. He had two twos. The center was a three, and eight, and a five of different suits. The pot started empty and Torchwick wasn't going to raise it. Everyone stayed and Ren played the next card which was a six. That caught Torchwick's attention. If he didn't fold he might get an inside straight if the last card was a four, but if it was anything else he'd have the second lowest possible hand in the game.

"I fold," Fox said, tossing his cards.

"Me too," Velvet said.

"I raise one piece of clothing," Coco said, removing her scarf and placing it in the center.

"I'll match," Yatsuhashi said, placing his boots in the center.

"Match," Nora said, placing her boots in the center.

"Fold," Ren said.

"I fold," Torchwick decided.

"I'll see that," Blake said, placing her boots in the center.

"I'll see too," Yang said, placing her jacket in the center.

"I'll… see it," Weiss hesitated, placing the belt Coco had loaned her in the middle.

Ren turned over the last card. It was another two. Coco, Yatsuhashi, Nora, Yang, Blake, and Weiss revealed their hands. Yang had the winning hand with a flush; two spades in her hand and by the end the center had three more spades. Blake had the worst hand with nothing Queen high. The rest had an assortment between.

Yang raked in her winnings and returned the jacket to her shoulders. Ren took the cards and shuffled a new hand.

"I'm a natural gambler," Yang said, "and great at holding my liquor."

"Do you get that from your uncle?" Coco asked.

"Hells yeah," Yang said.

Ren deal the next hand. Torchwick checked his hand to see a jack and a four of hearts. He peered over his cards to the center to see three tens rolled out.

"So we all have three of a kind," Nora giggled.

"Someone might have four," Fox whispered with a smirk.

Again, no one raised the pot this early into the round. Ren dealt the next card which was the Jack of clubs. Torchwick noted that he now had a full house.

"I raise the pot," Yang said, pushing her newly acquired boots into the center.

"I'll see that," Blake said, pushing the jacket Torchwick loaned her to the center.

"Me too," Velvet said, pushing her own jacket to the center.

"I fold," Fox said.

"I… mhh, I fold," Coco said, lowering her cards.

"I raise another piece of clothing," Weiss said, pushing her boots and socks into the center.

"I see that," Torchwick said, pushing his boots and socks in.

"I fold," Ren said.

"I fold," Yatsuhashi agreed.

"I'll see that," Nora said, pushing her jacket and socks to the center.

"I'll match," Yang said, pushing another pair of boots in.

Blake looked at her hand and to the center before saying, "Too risky, I fold."

"I'll match," Velvet said, pushing the scarf Coco had given her to the center.

Ren turned the last card over. It was a nine of clubs. Blake threw her hands in the air.

"That was it," Blake said. "The straight, not only that but since its spades a straight flush!"

Yang, Velvet, Torchwick, Nora, and Weiss revealed their hands. Torchwick had a full house, but Weiss hadn't been bluffing. She had the fourth ten in the deck and had the highest hand of four of a kind. Nora and Yang also had a full house, but lower than Torchwick's. Velvet had a flush, the lowest hand. Weiss collected her winnings as Ren began shuffling the next hand.

The game continued for a long while. The first player out was Weiss. After her win she faced nothing but losses and quit early with only her dress left; everything else had been won by one player or another. Fox would wind down with forced losses from to many folds but would win back enough with really high hands. He was second out when he couldn't win back his clothes and was left sitting in just his boxers. Yatsuhashi followed closely and also with just his boxers remaining.

Blake and Velvet held out a little longer but eventually lost to some well-done bluffs by Coco. The two of them sat in bra and panties; Blake indignant and Velvet thoroughly embarrassed. Ren proved a crafty card player and surprisingly adept at bluffing. He was also the only one to go toe to toe with Nora's all in gambling. She was out when she went all in on nothing King high and Ren called her on it with a pair of twos. She was left with just her bra and panties as well.

With only Yang, Ren, Torchwick, and Coc things began to get heated. The bluffs were intense and the mind games left the onlookers nervous about the game. Ren was starting to slip and lose some of his winnings. His final hand won Yatsuhashi's shirt and his own pants. He called it quits with just those two pieces and wrapped Nora in Yatsuhashi's oversized shirt.

That came down to the final three: Yang, Coco, and Torchwick. Torchwick was backed into a corner against the two who were starting to revert from drunk back to tipsy, and it showed in their gambling skills. If he was watching the match he'd bet on Yang to win; her skill with cards was far superior to his own or Coco's. He could tell she was only beginning to scratch the surface of her gambling potential. Had the stake been higher, Torchwick would've already been whipped out by Yang. Coco was also proving difficult because her play style had shifted from how it usually was during the mini-game; she was bolder which led Torchwick to fold on her bluffs more often.

"Next hand," Ren said, shuffling the deck.

He dealt the two cards to each player. Torchwick pulled up his hand and saw and Ace and a King of hearts. He looked at the center and saw the ten of hearts, the ten of clubs, and the seven of hearts. As of now, Torchwick was certain he had the worst hand.

"This is my win," Coco said boldly, "I bet five pieces of clothing."

"I'll see that," Yang said.

Torchwick checked his own winnings. He had seven pieces left. He looked to see that with her bet Coco had two pieces left. It was audacious to bet that high with only three cards in the center. Yang had nothing to fear with most of the clothes in her possession.

"I'll see that," Torchwick gambled.

He hoped Coco would back off on a bluff if both he and Yang called her. He also wasn't at risk of elimination if he only bet five of his seven. Ren played the next card: a Jack of hearts. Torchwick saw his chance was only in the next card being a Queen. Anything else and he'd have effectively nothing Ace high. He swallowed hard.

"Nervous?" Coco asked. "Let me ease those nerves with this: I'm all in."

Coco pulled off the last of her clothes and pushed them to the middle. She didn't flinch or show the slightest nerves the entire time.

"Oh ho," Yang said, "All in is just two more pieces, I'll see you."

Torchwick was in a corner. If the next card was a Queen he'd have a straight. However, they probably knew that. Anyone who saw a jack and a ten with someone refusing to back down was either bluffing or had a very high straight. Right now it was all bluff for Torchwick. He needed one of four cards in a deck of fifty two.

"Going for the straight?" Yang asked.

Torchwick turned to her.

"Be a shame if I had one of the queens you needed," Yang said.

Was she bluffing? Did she have the queen he needed to win? Should he fold? All these thoughts raced through Torchwick's head. Should he fold and try for a safer hand? Play for when they're weaker?

"This is pretty intense," Velvet muttered.

The room was still as Torchwick decided. He looked Yang in the eyes when he made his decision.

"I'll call," Torchwick said, taking off the last of his clothes and throwing them to the middle.

He could feel his face turning red. He wasn't as confident as the others in the room. Ren moved to reveal the last card. As he laid it down Torchwick released a breath he didn't realize he'd been holding. It was a Queen of Hearts. The three of them revealed their hands.

"Four of a kind," Coco said, revealing the two remaining tens.

"Neat, but I have a straight flush," Yang said, showing her hand to have nine and eight of hearts. "And now it's queen high. You should've folded Torchwick."

"Hehehe," Torchwick snickered. "You're ten years too young to be trying to play me like that."

He put his own cards down to reveal the Royal Flush that had fallen into his lap. Nora and Fox went ape shit screaming "Oh my god" and "get wrecked" when Torchwick revealed his hand. Coco threw her hands up in exasperation. Yatsuhashi sat silently nodding at the turn of events.

"Damn," Yang said. "You got so lucky."

With Coco now officially out it left just Yang and Torchwick. In a one on one Yang finished Torchwick off in no more than four hands. She took every last piece of clothing Torchwick had won from his royal flush faster than he'd won it.

"Hahaha," Yang laughed. "I'm the queen of your outfits."

"You payed us," Blake said. "Acting drunk the whole time."

"Nah," Yang said, "I'm pretty tipsy. You should see me gamble when I'm sober."

The party began to wind down and everyone had their clothes returned to them once Yang stopped lauding her victory over them. As Torchwick was getting ready to leave the dorm Coco stopped him.

"What's up?" Torchwick asked.

Before responding she gave him a quick kiss on the lips. Her lips were softer than he was expecting. He felt her lips forming a smile as she pulled away from him. Over her shoulder he saw Nora shaking Ren and turning his head towards the scene. Velvet had covered her mouth with her hands. Yang was giving him a smug smile. The rest didn't seem to care in the slightest.

"Thanks for coming today," Coco said.

The world faded and reset itself to the start of the game. Torchwick opened his notebook and marked Coco as being romanced once.


End file.
